Direct Palladium/Carboxylic Acid‐Catalyzed Allylation of Anilines with Allylic Alcohols in Water.

Yang, Shyh-Chyun; Hsu, Yi‐Chun; Gan, Kim-Hong

doi:10.1002/chin.200633096

Cited by 1 publication

(1 citation statement)

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“…Based on the classification of Sharpless, the reactions are named as “on water” protocols when some of the reactants are insoluble in the aqueous medium [ 29 , 30 , 31 , 32 , 33 , 34 , 35 ]. It is important to note that a few metal-catalyzed examples have been also developed “on water”, such as with gold(III) [ 36 , 37 ], In(III) [ 38 ] or Pd(0) [ 39 , 40 , 41 , 42 , 43 ]. However, high temperature or the use of a co-catalyst or an acid additive is necessary.…”

Section: Introductionmentioning

confidence: 99%

Direct Substitution of Alcohols in Pure Water by Brønsted Acid Catalysis

Ortiz

Herrera

2017

Molecules

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With the increasing concern for sustainability, the use of environmentally friendly media to perform chemical processes has attracted the attention of many research groups. Among them, the use of water, as the unique solvent for reactions, is currently an active area of research. One process of particular interest is the direct nucleophilic substitution of an alcohol avoiding its preliminary transformation into a good leaving group, since one of the by-products in this approach would be water. The direct substitution of allylic, benzylic, and tertiary alcohols has been achieved through SN1-type reactions with catalytic amounts of Brønsted or Lewis acids; however, organic solvents are often required. In this review, the pioneering SN1 approaches performed in pure water and in the absence of a metal based Lewis acid are compiled and discussed.

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